3,5-Diethyl-4-aminophenol | 108451-25-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,5-Diethyl-4-aminophenol
• 英文别名: 4-amino-3,5-diethylphenol；3,5-diethyl-4-amino-phenol；3,5-Diaethyl-4-amino-phenol；2,6-diethyl-4-hydroxyaniline
• CAS: 108451-25-8
• 化学式: C₁₀H₁₅NO
• 分子量: 165.235
• InChiKey: DVDARSFBQPNPGW-UHFFFAOYSA-N

物化性质

• 沸点：
  325.5±30.0 °C(Predicted)
• 密度：
  1.060±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,5-Diethyl-4-aminophenol 在 lead(IV) acetate 、 silica gel 作用下， 以 正己烷 、 乙酸乙酯 为溶剂， 反应 0.17h， 生成 2,6-二乙基-1,4-苯醌
  参考文献：
  名称：

  Dialkylquinoneimine metabolites of chloroacetanilide herbicides induce sister chromatid exchanges in cultured human lymphocytes

  摘要：

  Some of the most widely-used herbicides are the chloroacetanilides exemplified by alachlor and butachlor (derived from 2,6-diethylaniline) and metolachlor and acetochlor (synthesized from 2-ethyl-6-methyIaniline). This investigation tests the hypothesis that the previously-observed oncogenicity of these herbicides is due to genotoxic intermediates such as diethylbenzoquinoneimine, a purported alachlor metabolite. Syntheses are reported here for the corresponding 2,6-dialkylbenzoquinoneimines, selected chloroacetyldialkylbenzoquinoneimines and several other candidate or known metabolites. The possible mutagenicity of diethylbenzoquinoneimine was tested in Salmonella typhimurium strains TA98 and TA100 with a weakly-positive response in the TA100 strain indicating induction of base-pair substitution mutations. The frequency of sister chromatid exchange (SCE) in Chinese hamster ovary cells was increased by alachlor at 10 mu M and diethylaniline but not ethylmethylaniline at 30 and 3 mu M Isolated and cultured peripheral lymphocytes (mostly T cells) were used from two human donors to study the effects of the chloroacetanilides and their metabolites on primary human cells. In tests at 10 mu M, the SCE frequency was increased by alachlor and possibly acetochlor but not by butachlor, metolachlor, dimethachlor (a 2,6-dimethyl analog) and dimethenamid (an analog based on 2,4-dimethyl-3 -thienylamine). At 0.3 mu M in cultured human lymphocytes, alachlor, the corresponding chloroacetanilide( N-dealkyl-alachlor) and aniline metabolites (and their 4-hydroxy derivatives), and diethylbenzoquinone were inactive or active in only one of the two donors whereas at 0.1-0.3 mu M the SCE ratio for treated cells divided by the controls was always higher for diethylbenzoquinoneimine than for ethylmethyl- and dimethylbenzoquinoneimines. All the tested compounds were toxic to lymphocytes, but the depression of the mitotic index and increased duration of the cell cycle were not directly linked with SCE induction. Previous investigations have suggested that chloroacetanilide herbicides such as alachlor derived from 2,6-dialkylanilines are metabolized to 2,6-dialkylbenzoquinoneimines and the present study provides the first direct evidence that these metabolites are genotoxic in human lymphocytes. (C) 1997 Elsevier Science B.V.

  DOI：

  10.1016/s1383-5718(97)00163-0
• 作为产物：
  描述：

  2,6-二乙基苯胺 在 rat liver S-9 、 烟酰胺腺嘌呤双核苷酸磷酸盐 、 magnesium chloride 作用下， 生成 3,5-Diethyl-4-aminophenol
  参考文献：
  名称：

  酶法合成4-氨基-3,5-二乙基苯基硫酸盐（一种甲草胺的啮齿动物代谢产物）。

  摘要：

  大鼠肝脏组织匀浆用于将2,6-二乙基苯胺（DEA）体外酶促转化为重要的甲草胺代谢物4-氨基-3,5-二乙基苯基硫酸盐（ADEPS），该产物也作为放射性标记的标准品生成，用于代谢研究。啮齿动物中ADEPS的形成与甲草胺啮齿动物致癌作用中涉及的其他反应性代谢产物的产生相关，因此非常需要可靠地获得ADEPS标准。（14）C-DEA被大鼠肝微粒体氧化为（14）C-4-氨基-3,5-二乙基苯酚，通过添加磷酸硫酸盐转移酶辅因子腺苷3'-磷酸盐-5'将其进一步转化为ADEPS。 -磷酸二氢盐。Microprobe NMR与高分辨率质谱联用，可以完全表征所得的（14）C-ADEPS并确认其结构。

  DOI：

  10.1021/jf980654f

文献信息

• Hapten Design in the Development of Competitive Enyme-Linked Immunosorbent Assays for Genotoxic Metabolites of Alachlor
  作者：Daniel M. Tessier、J. Marshall Clark

  DOI：10.1021/jf990087b

  日期：1999.9.1

  products of the chloroacetanilide herbicide alachlor. CDA, HDA, and alachlor are ground and surface water contaminants. CDA and HDA are genotoxic in bacterial and mammalian test systems. This paper reports hapten design in the development of two competitive enzyme-linked immunosorbent assays (cELISA) for the detection of CDA and HDA. Chloroacetanilide herbicides and other alachlor metabolites that

  乙酰苯胺化合物2-氯-2'，6'-二乙基乙酰苯胺（CDA）和2-羟基-2'，6'-二乙基乙酰苯胺（HDA）是氯乙酰苯胺除草剂甲草胺的环境降解产物。CDA，HDA和甲草胺是地下水和地表水污染物。CDA和HDA在细菌和哺乳动物测试系统中具有遗传毒性。本文报道了用于检测CDA和HDA的两种竞争性酶联免疫吸附测定（cELISA）的半抗原设计。环境样品中可能存在的氯乙酰苯胺除草剂和其他甲草胺代谢产物不会与CDA和HDA的检测发生交叉反应。从水性样品中固相萃取CDA和HDA残留物可得到1000倍的浓缩系数，这两种测定的有效检测限均为15 pg / mL。cELISA的特异性要求在半抗原设计中保留乙酰苯胺部分的取代度。半抗原合成策略适用于其他氯乙酰苯胺除草剂（即乙草胺，丁草胺，甲草胺和丙草胺）的代谢产物。
• Substituted thioureas, isothioureas and carbodiimides and their use as
  申请人：Ciba-Geigy Corporation

  公开号：US04914098A1

  公开（公告）日：1990-04-03

  Substituted N-phenylthioureas, N-phenylisothioureas and N-phenylcarbodiimides of formula ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.8 cycloalkyl, polycyclic alkyl containing a total of 7 to 10 carbon atoms, C.sub.1 -C.sub.12 alkyl which is substituted by 1 to 12 halogen atoms, C.sub.1 -C.sub.4 alkyl which is substituted by one or two C.sub.3 -C.sub.6 cycloalkyl radicals, alkoxyalkyl containing a total of 3 to 10 carbon atoms, C.sub.1 -C.sub.5 alkyl which is substituted by a phenyl radical, C.sub.1 -C.sub.5 alkyl which is substituted by a phenyl radical which is in turn substituted by one or two members selected from the group consisting of halogen, methyl, methoxy and ethoxy; or is C.sub.3 -C.sub.10 -alkenyl or C.sub.3 -C.sub.10 alkynyl, R.sub.2 is hydrogen or C.sub.1 -C.sub.4 alkyl, R.sub.3 is C.sub.1 -C.sub.4 alkyl, R.sub.4 is hydrogen or C.sub.1 -C.sub.4 alkyl, and R.sub.5 is a defined nitrogen-containing heterocyclic radical, and Z is a group selected from ##STR2## and salts thereof, the preparation of said compounds and compositions containing them for use in pest control.

  公式为##STR1##其中，R.sub.1是C.sub.1-C.sub.12烷基，C.sub.3-C.sub.8环烷基，含有7到10个碳原子的多环烷基，被1到12个卤素原子取代的C.sub.1-C.sub.12烷基，被一个或两个C.sub.3-C.sub.6环烷基基团取代的C.sub.1-C.sub.4烷基，总碳原子数为3到10的烷氧基烷基，被苯基取代的C.sub.1-C.sub.5烷基，被一个或两个成员中的一个取代的苯基，所述成员由卤素，甲基，甲氧基和乙氧基组成；或者是C.sub.3-C.sub.10-烯基或C.sub.3-C.sub.10炔基，R.sub.2是氢或C.sub.1-C.sub.4烷基，R.sub.3是C.sub.1-C.sub.4烷基，R.sub.4是氢或C.sub.1-C.sub.4烷基，R.sub.5是一个定义的含氮杂环基团，Z是从##STR2##和其盐中选择的一个基团，所述化合物的制备和含有它们的组合物用于害虫控制。
• Hydroxyaryliminoaryl carbamates, imine bisphenols and derivatives thereof useful as insecticidal compositions
  申请人：UNION CARBIDE CORPORATION

  公开号：EP0067503A1

  公开（公告）日：1982-12-22

  This invention relates to hydroxyarylalkyleneaminoaryl carbamate compounds, imine bisphenols and derivatives thereof and to their preparation. This invention is also directed to insecticidal compositions comprising an acceptable carrier and an insecticidally effective amount of a hydroxyarylalkyleneaminoaryl carbamate compound or derivative of this invention as well as to a method of controlling insects by subjecting them to an insecticidally effective amount of a hydroxyarylalkyleneaminoaryl carbamate compound or derivative of this invention.

  本发明涉及羟基芳烷基氨基芳基氨基甲酸酯化合物、亚胺双酚及其衍生物及其制备。本发明还涉及由可接受的载体和杀虫有效量的本发明羟基芳烷基氨基甲酸酯化合物或衍生物组成的杀虫组合物，以及通过使昆虫受到杀虫有效量的本发明羟基芳烷基氨基甲酸酯化合物或衍生物来控制昆虫的方法。
• Therapeutics for killing bacteria
  申请人：OSTRO RES LAB INC

  公开号：US02040183A1

  公开（公告）日：1936-05-12
• US4147804A
  申请人：——

  公开号：US4147804A

  公开（公告）日：1979-04-03